I'm sure I'm not the only one thinking abou gettign a smartphone. I've had my eye on the Blackberry personally (seeing as it looks like the best option on TMobile). But this whole quest to find a good smartphone has me thinking about a lot of things.
Which blackberry? The pearl is supposed to be awesome, its very tiny. The only real issue is the suretype keyboard, which sort of "guesses" which of the two letters you wanted, and then matches from there. It's supposed to be very smart, but just consider that it might be slow going for a few day on it. Play with one in-store and try it out.
I dig the new Samsung Blackjack but it's under Cingular and I don't know if buying an unlocked version of the phone would work with TM.
Then I thought--even if I got a new sleek techno-phone, how difficult would it be to get those nice features to work with my mac.
The unlocked version would be hella expensive. Also, the blackjack is a damn cool phone, but one of it's biggest selling points is that it works with 3G data on Cingular, something that won't work on T-Mobile since they do not have a broadband data network. If you aren't going to use it on Cingular, I'd recommend you get a T-Mo Dash, which is effectively the same as a Blackjack but with a slightly bigger screen and wifi-same operating system, qwerty kb, etc. Also, if you need to use T-Mo, it would be significantly better bang for your buck than an unlocked BJ.
Also a good choice would be a Treo. Unless you REALLY want Windows Mobile and are looking to drop 600+ dollars, your only unlocked Treo option would be a 680, which is 399 unlocked from Palm. I've heard of many people using it with no issues on T-Mo. As a rule, unlocked phones should work fine on either Cingy or T-Mo, but you might need to call and get the settings for internet browsing if your SIM card can't get the phone to d/l them automatically.
As the earlier poster mentioned, Missing Sync works very well, and there are versions for both Palm and WinMob. If you want to just sync your calendar, contacts and an occasional program on Palm OS, Missing Sync is probably too much. If you want to play mp3s, etc, Missing Sync has a much nicer and cleaner way of getting that stuff on Macs.
You will need Missing Sync no matter what for WinMob, and there's another program (Pocket Mac, I think) that does Blackberry-->Mac sync.
I've done some Winmob syncing on an old ibook, and it's not bad. It's actually a very smooth process, so except for the occasional program wrapped in .exe, Missing Sync should handle it fine. And for those, if you email the developer really nicely, they'll usually send the .cab file from what i've read. (.cab is the Windows Mobile file extension.)
So I pose these questions to you Mac/tech savvy folks out there who've dealt with compatibility and all the other issues with finding a good smartphone.
Hope this was helpful. FYI, I use a Palm Treo 650, and any issues I've had have been across the board all OS issues, or user error.